Winsted, CT 55+ active adult communities & homes for sale

77 communities near Winsted

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Clockmaker's Hill

$100Ks

Clockmaker's Hill, Winsted, CT

Resale Only | 55+ age-restricted | Built 2005 - 2014 | 38 homes

3 rating (2 reviews)

Heritage Hills

$300Ks - $900Ks

Heritage Hills, Somers, NY

Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes

3.6 rating (7 reviews)

Heritage Village

$200Ks - $500Ks

Heritage Village, Southbury, CT

Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes

Rivington

$400Ks - $600Ks

Rivington, Danbury, CT

New and Resale | Age-targeted | Built 2006 - present | 1,050 homes

4 rating (1 reviews)

Jefferson Village

$200Ks - $600Ks

Jefferson Village, Yorktown Heights, NY

Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes

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Questions? Call us: (860) 909-8066

Oronoque Village

$300Ks - $600Ks

Oronoque Village, Stratford, CT

Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes

The Village at Oxford Gre...

$500Ks - $600Ks

The Village at Oxford Gre..., Oxford, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes

Spring Lake Village

$200Ks

Spring Lake Village, Southington, CT

Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes

Regency at Prospect

$300Ks - $500Ks

Regency at Prospect, Prospect, CT

Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes

The Retreat at Carmel

$400Ks - $600Ks

The Retreat at Carmel, Carmel, NY

Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes

Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.

Overlook

$600Ks - $800Ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

Meadow Brook Estates

$500Ks

Meadow Brook Estates, Oxford, CT

Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes

The Summit at Bethel

$600Ks

The Summit at Bethel, Bethel, CT

Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes

4.9 rating (14 reviews)

Chatfield Farms

$500Ks - $600Ks

Chatfield Farms, Beacon Falls, CT

New Construction | 55+ age-restricted | Built 2014 - present | 231 homes

Regency at Wappinger

$600Ks - $700Ks

Regency at Wappinger, Wappingers Falls, NY

Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes

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Questions? Call us: (860) 909-8066

The Powder Forest Homes

$600Ks - $700Ks

The Powder Forest Homes, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes

5 rating (1 reviews)

Newtown Woods

$400Ks - $500Ks

Newtown Woods, Newtown, CT

New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes

Beckley Farms

$300Ks - $400Ks

Beckley Farms, Berlin, CT

New and Resale | 55+ age-restricted | Built 2010 - present | 170 homes

Regency at Fishkill

$400Ks - $500Ks

Regency at Fishkill, Fishkill, NY

Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes

South Pond Village

$100Ks - $200Ks

South Pond Village, Bloomfield, CT

Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes

Fieldstone Village

$500Ks - $800Ks

Fieldstone Village, Orange, CT

Resale Only | 55+ age-restricted | Built 2010 - 2018 | 142 homes

North Woods of Colchester

$500Ks

North Woods of Colchester, Colchester, CT

New and Resale | 55+ age-restricted | Built 2007 - present | 140 homes

Fairview at Oxford Greens

$600Ks

Fairview at Oxford Greens, Oxford, CT

New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes

3.5 rating (2 reviews)

Harvest Pointe

$800Ks - $3Ms

Harvest Pointe, Cutchogue, NY

New Construction | 55+ age-restricted | Built 2017 - present | 124 homes

Newbury Village

$600Ks - $700Ks

Newbury Village, Brookfield, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes

Want to learn more about 55+ communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

The Gardens of Wilbraham

$500Ks

The Gardens of Wilbraham, Wilbraham, MA

New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes

O'Meara Farm

$400Ks - $500Ks

O'Meara Farm, Farmington, CT

Resale Only | 55+ age-restricted | Built 1998 - 2005 | 104 homes

The Bridges at Oxford Gre...

$600Ks

The Bridges at Oxford Gre..., Oxford, CT

New Construction | 55+ age-restricted | Built 2025 - present | 99 homes

Liberty at Newtown

$300Ks - $400Ks

Liberty at Newtown, Newtown, CT

Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes

Applegate Estates

$500Ks - $400Ks

Applegate Estates, Southington, CT

New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 homes

Founders Village

$500Ks - $600Ks

Founders Village, Southold, NY

Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 homes

Pond Spring Village

$300Ks

Pond Spring Village, Beacon Falls, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes

Glassbury Court at Cold S...

$500Ks - $700Ks

Glassbury Court at Cold S..., Cold Spring, NY

Resale Only | 55+ age-restricted | Built 2009 - 2014 | 90 homes

5 rating (1 reviews)

Paris Square

$400Ks - $700Ks

Paris Square, Northvale, NJ

New and Resale | 55+ age-restricted | Built 2000 - present | 88 homes

Castle Heights of Cheshir...

$500Ks - $600Ks

Castle Heights of Cheshir..., Cheshire, CT

Resale Only | 55+ age-restricted | Built 2007 - 2022 | 88 homes

Want to learn more about 55+ communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

Bartlett Hill

$500Ks

Bartlett Hill, Portland, CT

Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes

Baldwin Station

$400Ks

Baldwin Station, Milford, CT

Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes

5 rating (2 reviews)

Benson Woods

$400Ks - $600Ks

Benson Woods, Middlebury, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 79 homes

Shaker Heights

$400Ks - $500Ks

Shaker Heights, Enfield, CT

New Construction | 55+ age-restricted | Built 2018 - present | 77 homes

5 rating (3 reviews)

Founders Ridge

$500Ks - $600Ks

Founders Ridge, Middletown, CT

New Construction | 55+ age-restricted | Built 2017 - present | 75 homes

1...2

The Gardens of Wilbraham

116 CHERRY DR # 116, WILBRAHAM, MA, 0109..., Wilbraham, MA 01095

$515,000

2 beds

2 baths

1,634 sq ft

Condo

116 CHERRY DR # 116, WILBRAHAM, MA, 0109...

Community: The Gardens of Wilbraham

The Gardens of Wilbraham

32 LODGE LN # 32, WILBRAHAM, MA, 01095, Wilbraham, MA 01095

$565,000

2 beds

2 baths

1,610 sq ft

Condo

32 LODGE LN # 32, WILBRAHAM, MA, 01095

289 AGAWAM DR B, STRATFORD, CT, 06614

Community: Oronoque Village

Want to learn more about 55+ communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

New Heritage Village

25 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$449,000

2 beds

2 baths

1,447 sq ft

Condo

25 HERITAGE CRST C, SOUTHBURY, CT, 06488

Community: Heritage Village

Rivington

$499,900

2 beds

2 baths

1,229 sq ft

Condo

1 RIVINGTON WAY UNIT 201, DANBURY, CT, 0...

Community: Rivington

New Oronoque Village

133 BANNOCK LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$629,900

1 beds

3 baths

1,438 sq ft

Condo

133 BANNOCK LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

966 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$350,000

2 beds

2 baths

1,398 sq ft

Condo

966 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

876 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$390,000

2 beds

2 baths

1,398 sq ft

Condo

876 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

736 QUINNIPIAC LN B, STRATFORD, CT, 0661..., Stratford, CT 06614

$475,000

1 beds

3 baths

1,426 sq ft

Condo

736 QUINNIPIAC LN B, STRATFORD, CT, 0661...

Community: Oronoque Village

Evergreen

34 WOODSBORO CIR # 34, CROMWELL, CT, 064..., Cromwell, CT 06416

$519,900

2 beds

2 baths

1,758 sq ft

Condo

34 WOODSBORO CIR # 34, CROMWELL, CT, 064...

Community: Evergreen

New Heritage Village

953 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$279,900

1 beds

1 baths

928 sq ft

Condo

953 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Chatfield Farms

18 FIELDSTONE LN # 18, BEACON FALLS, CT,..., Beacon Falls, CT 06403

$599,000

2 beds

3 baths

2,719 sq ft

18 FIELDSTONE LN # 18, BEACON FALLS, CT,...

Community: Chatfield Farms

Heritage Village

98 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$309,900

2 beds

2 baths

1,044 sq ft

Condo

98 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Want to learn more about 55+ communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

Oronoque Village

664 OSAGE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$549,900

1 beds

3 baths

1,438 sq ft

Condo

664 OSAGE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Newtown Woods

603 BROOKSIDE CT # 603, NEWTOWN, CT, 064..., Newtown, CT 06470

$489,000

2 beds

2 baths

1,504 sq ft

Condo

603 BROOKSIDE CT # 603, NEWTOWN, CT, 064...

Community: Newtown Woods

Newtown Woods

433 BROOKSIDE CT 433, NEWTOWN, CT, 06470, Newtown, CT 06470

$500,000

2 beds

2 baths

1,504 sq ft

Condo

433 BROOKSIDE CT 433, NEWTOWN, CT, 06470

Community: Newtown Woods

New The Village at Buckingham

8 KENINGTON RD # 8, AVON, CT, 06001, Avon, CT 06001

$599,900

3 beds

3 baths

2,430 sq ft

Condo

8 KENINGTON RD # 8, AVON, CT, 06001

Community: The Village at Buckingham

Heritage Village

123 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$399,900

2 beds

2 baths

1,398 sq ft

Condo

123 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

862 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$499,900

3 beds

2 baths

1,716 sq ft

Condo

862 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

Oronoque Village

35 ALGONQUIN LN D, STRATFORD, CT, 06614, Stratford, CT 06614

$399,000

2 beds

2 baths

1,300 sq ft

Condo

35 ALGONQUIN LN D, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Village

60 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$285,000

2 beds

2 baths

1,365 sq ft

Condo

60 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

701 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$329,000

3 beds

2 baths

1,716 sq ft

Condo

701 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Spring Lake Village

373 LAKEVIEW DR # 373, SOUTHINGTON, CT, ..., Southington, CT 06489

$259,900

2 beds

2 baths

1,188 sq ft

Condo

373 LAKEVIEW DR # 373, SOUTHINGTON, CT, ...

413 MULLIGAN DR # 413, OXFORD, CT, 06478

Condo

10 LUCIUS CT # 10, MILFORD, CT, 06461

Community: Gloria Commons

1 2 3…4

Frequently Asked Questions

What size 55+ communities are there in Winsted?

In Winsted, there is 1 small community with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Winsted?

The smallest 55+ community in Winsted has 38 homes, the largest has 38 homes, and the average community consists of 38 homes.

Are there gated 55+ communities in Winsted?

No, there are no gated 55+ communities in Winsted.

Want more information about active adult communities around Winsted?

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Call us: (860) 909-8066

77 communities near Winsted

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Winsted, CT 55+ active adult communities & homes for sale

77 communities near Winsted

142 homes near Winsted

2 beds

2 baths

1,634 sq ft

Condo

2 beds

2 baths

1,610 sq ft

Condo

1 beds

3 baths

1,620 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

3 baths

1,620 sq ft

Condo

2 beds

2 baths

1,447 sq ft

Condo

2 beds

2 baths

1,229 sq ft

Condo

1 beds

3 baths

1,438 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

1 beds

3 baths

1,426 sq ft

Condo

2 beds

2 baths

1,758 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

2 beds

3 baths

2,719 sq ft

2 beds

2 baths

1,044 sq ft

Condo

1 beds

3 baths

1,438 sq ft

Condo

2 beds

2 baths

1,504 sq ft

Condo

2 beds

2 baths

1,504 sq ft

Condo

3 beds

3 baths

2,430 sq ft

Condo

2 beds

2 baths